Ethyl ketone → 5-Fluoro-3-(3-hydroxypent-3-yl)[O-(3,4-dimethoxybenzyl)]phenol

HRID 260421

反応式

HRID 260421 の反応式
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:3]=1.[Li]CCCC.[CH3:26][CH2:27][C:28](=[O:31])[CH2:29][CH3:30]>C1COCC1>[F:8][C:6]1[CH:7]=[C:2]([C:28]([OH:31])([CH2:29][CH3:30])[CH2:27][CH3:26])[CH:3]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:5]=1

参加物

5

反応物 3

HCID 7288Ethyl ketoneHCID 194269851-Bromo-3-(3,4-dimethoxybenzyloxy)-5-fluorobenzeneHCID 178418339Butyllithium

生成物 1

HCID 701948305-Fluoro-3-(3-hydroxypent-3-yl)[O-(3,4-dimethoxybenzyl)]phenol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-bromo-3-(3,4-dimethoxybenzyloxy)-5-fluorobenzene (Step 1) (1.02 g) in THF (10 mL) at -78° C. was added n-BuLi (1.5 mL of a 2.2M solution) dropwise. After 30 min. 3-pentanone (0.33 mL) was added and after 30 min. the bath was removed and the mixture stirred for 10 min. The reaction mixture was quenched with NH4OAc buffer and extracted with EtOAc. The organics were dried (MgSO4) and concentrated. Chromatography of the residue (silica gel; hexane/EtOAc (3:1) provided the title compound as a colorless oil.

後処理

  1. customwas removed
  2. customThe reaction mixture was quenched with NH4OAc buffer
  3. extractionextracted with EtOAc
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8c5570ddf3ee4ec082c49fe9472d1e9a
出典データセット
uspto-grants-1996_06
特許番号
US05527827

関連ノート

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